EPISODE · Jul 18, 2025 · 1H 5M
1172 - "Olivia" is a Crossdresser who's Wife is Down with him Crossdressing
from Strictly Anonymous Confessions · host Kathy Kay
Olivia is a crossdresser who has a wife who’s down with his crossdressing. Tune in to hear alll the details including the friend who got him to dress up the first time and how he felt when dressed up, how and when he started dressing up at home and where he got his clothes from, how and why he was confused about being into wearing female clothing, down, how he got caught dressing up and how his parents reacted, how he defines himself sexually and his one hook up with a guy off Grindr he has in college and exactly what went down, how and why he told his first gf about how fetish and how she reacted at first and then how her feelings changed over time, how he told his next gf and how she reacted at first, the questions she had for him and how she felt the first time she saw him dressed, how often he dresses up at home now that’s he’s married and she’s down with it, how often he gets to be intimate with his wife while dressed, how he’s still into guys but why he won’t hook up with one and how he keeps the urges down, where he buys his clothing now, how he sometimes wonder if he’d be happier if he was a girl but why he’s still content in his life plus a whole lot more. **To see anonymous a pics of my guests + get TONS of exclusive HOSER and/or CROSSDRESSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [email protected] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://liferx.md Start your transformation now and get $50 OFF your first month, use code: ANONYMOUS https://beducate.me/pd2520-anonymous Use code: ANONYMOUS to get 50% off your yearly pass plus get a 14-day money-back guarantee https://vb.health To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website: http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Olivia is a crossdresser who has a wife who’s down with his crossdressing. Tune in to hear alll the details including the friend who got him to dress up the first time and how he felt when dressed up, how and when he started dressing up at home and where he got his clothes from, how and why he was confused about being into wearing female clothing, down, how he got caught dressing up and how his parents reacted, how he defines himself sexually and his one hook up with a guy off Grindr he has in college and exactly what went down, how and why he told his first gf about how fetish and how she reacted at first and then how her feelings changed over time, how he told his next gf and how she reacted at first, the questions she had for him and how she felt the first time she saw him dressed, how often he dresses up at home now that’s he’s married and she’s down with it, how often he gets to be intimate with his wife while dressed, how he’s still into guys but why he won’t hook up with one and how he keeps the urges down, where he buys his clothing now, how he sometimes wonder if he’d be happier if he was a girl but why he’s still content in his life plus a whole lot more. **To see anonymous a pics of my guests + get TONS of exclusive HOSER and/or CROSSDRESSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [email protected] or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://liferx.md Start your transformation now and get $50 OFF your first month, use code: ANONYMOUS https://beducate.me/pd2520-anonymous Use code: ANONYMOUS to get 50% off your yearly pass plus get a 14-day money-back guarantee https://vb.health To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website: http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices
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1172 - "Olivia" is a Crossdresser who's Wife is Down with him Crossdressing
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